The idea first took hold while entertaining Charles, a business partner and fellow entrepreneur, at my estate. We lounged in the saloon, sipping bourbon and chatting while Isabelle took a brief respite from her bar-tending duties to service me.

Charles looked over us in distaste. “It's a bit garish to have just one servant for sexual relief, isn't it?” He asked delicately. “How do you keep your guests entertained?” He added, turning his nose up haughtily.

I frowned, thinking it over as Isabelle obediently kept my cock warm, buried down in the tight moisture of her throat. “I guess I hadn't really considered it.” I admitted. “Isabelle's always been able to take care of my needs pretty well.” I added proudly.

“She's just one woman.” Charles said with a laugh. “I think you need to hire more help.” He added.

“Isabelle isn't just any woman, though.” I said defensively, eyebrow furrowing. “Still, you might be on to something.” I added thoughtfully.

“Isabelle. Be so kind as to give our guest a show while you service me.” I command curtly.

Isabelle withdraws from my length, detaching from the tip of my cock with a wet, sticky \pop.\** “As you wish, master~” She says, lifting her skirt up past her asscheeks and wiggling her ass enticingly before she descends back onto my cock, moaning erotically and drooling all over my nutsack.

Charles takes his cock out and begins to stroke lightly for a time. After a couple minutes, Isabelle again withdraws from me, her doe eyes on mine.

“Although, if I may be so bold, master~” Isabelle begins. “Might it not be more conducive to our guest's relaxation for me to take his shaft in my hand and stroke his penis while I warm you with my throat?” She asks.

Fair point.

I nod on, gesturing for her to place her gloved hand on Charles, and relieve the two of us in unison until I climax down her throat and Charles makes a wet, sticky mess on her outfit for her to clean up.

---

After dinner, Charlie takes off, and I beckon Isabelle over.

“Yes, master?” She asks.

I size her up before speaking. “I've been thinking, Isabelle. How would you like for me to bring on another maid for you to train, to help in your duties?” I ask.

Isabelle's wide eyes light up. “Truly, Master? A sister-in-service?” She exclaims. “How wonderful, Master!” She adds, clapping her hands together in girlish enthusiasm.

“Kind of. The women around here are vultures. You're the only woman I trust.” I admit. “Your job is to go to the city and find a feminine boy to bring to the mansion, to transform into your twin. You have my permission to use any methods within reason to subdue or convince them.” I command.

Isabelle nods emphatically. “Very good, Master~” She says, with a hint of a wicked gleam behind her large, innocent eyes. “I shall begin the necessary preparations and begin my search immediately.” She adds. “...Unless you have need for me before I depart?” She asks.

I grin. “As a matter of fact, I do.” I say, bending her over a chair and lifting her apron. “I'm going to give you a parting gift, so you're capable of providing our new friend with a taste of what it means to serve me.” I say as I bury my cock into her cunt, thrusting stiffly.

“Very good, Master~” Isabelle replies, her breathing intensifying and giving way to lewd moans and squeals of delight as her eager slit swallows up my thick shaft.

----------

Hey! I would like to play a Master who turns a cute boy into an obedient sissy servant with the help of his beautiful, capable maid. I'm really looking to open this up, so I'm interested in anyone playing. I'll retain sole control of the Master, but I'm happy to divvy up/share control of the others, depending on your tastes.

For any women interested, I'll admit that I did write out Isabelle to have a particular persona, more to convey the tone I'm interested in, but everything, including name is up for discussion.

For any boys interested, I would say that this prompt will lean heavily on feminization. Having kinks for chastity and ruined orgasms will put you ahead of the competition. Any discussion of potential rewards for good service may be taken up with Isabelle, before being run by me to give the final word.

Be well!

Kinks: Lipstick marks, sloppy oral, facials, creampies, throatpies, intercourse and outercourse, every “job” you can think of, cuddlefucks, watersports, spitroast, blowbang, DP/gangbang, aftercare, kissing, cockwarming, CFNM, bimbofication, cheating and homewrecking sluts, dressup/cosplay/slutty outfits/outfit control, blatant teasing, degradation, seduction, excessive cum, cum-play, multiple loads and much more!!

Limits: Futa, anthro/non-human, celeb, vore, gore, snuff, scat.